Deals on vacations and trips to Cumberland County

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A lighthouse, a white house with a red roof, and rocky coastline at sunset.

Portland

Vacations
Portland

Cumberland County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,297, price is now $696 per person
$696
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $2,900, price is now $1,709 per person
$1,709
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Save 100% on your flight
Price was $2,325, price is now $1,394 per person
$1,394
per person
Sep 23 - Sep 30
found 18 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $1,508, price is now $907 per person
$907
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
This apartment features a gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the a rooftop terrace and perks like free self parking.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $3,250, price is now $1,980 per person
$1,980
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

Top Cumberland County hotels deals

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $160 total per night
$160 total
Jul 27 - Jul 28
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $198 total per night
$198 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free on-the-go breakfast each morning.
Pool
Breakfast included
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
$144 nightly
The price is $159 total per night
$159 total
Aug 2 - Aug 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.
Pool
Hot Tub
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$348 nightly
The price is $385 total per night
$385 total
Jul 26 - Jul 27
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.
Hot Tub
Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Free Cancellation
$293 nightly
The price is $325 total per night
$325 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A safe deposit box is provided and the front desk is staffed around-the-clock.
Pet friendly
Free WiFi
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$421 nightly
The price is $465 total per night
$465 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Pet friendly
Free WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Cumberland County attractions

A multi-story brick building with a large arched window and a sign that reads "STATE".

State Theatre

8.8/10 (392 reviews)
You can make plans for a show at State Theatre during your trip to Portland. Experience the area's acclaimed theater scene and entertainment choices.
See properties

Photos of local treasures

Browse Cumberland County vacation photos for more inspiration

A coastal lighthouse with red-roofed houses, rocky shoreline, and the ocean.
A lighthouse on a rocky outcrop with a red-roofed building nearby, a clear blue sky, and the ocean in the background.
A lighthouse, a red-roofed house, and rocky coastline.
A lighthouse, rocky coastline, and a house by the sea.
A lighthouse, rocky shoreline, and a house by the sea.

Frequently asked questions

How much are vacation packages to Cumberland County?
$696 is all you'll need for a memorable break in Cumberland County. Bundle your flights and hotel into a Travelocity package and see how much the savings pile up. With such good prices, you'll want to start packing your bags now!
Where can I get the best vacation package deals for Cumberland County?
Look no further than Travelocity. With as many as 400 airlines and 1,000,000 properties across the globe, it's a breeze to find a Cumberland County package deal that satisfies your wanderlust.
Why should I purchase my Cumberland County vacation package via Travelocity?
Travel should be about making cherished new memories and forgetting all your worries — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.
Will I save money on my Cumberland County car rental if I combine it with a hotel or flight?
Bundling your bookings into a Cumberland County vacation package will certainly save you money. You can book a car and flight; a car, flight and hotel; or a hotel and car. You won't find a better way to discover the greater Cumberland County region than with your own set of wheels. You can also add experiences and tours to your Travelocity package.
Which airport is best for Cumberland County?
Take your pick of Portland Intl. Jetport Airport (PWM) or Augusta State Airport (AUG). They are the main airports for those traveling to and from Cumberland County.
What is there to do in Cumberland County?
Cumberland County has hidden surprises around every corner, however ensure you get to Portland Museum of Art and University of Southern Maine while you're in town. These two attractions are very popular with visitors to the region.

Where to stay in Cumberland County: Best areas for travelers

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